3-(2-hydroxy-4-isopropyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one | 1434878-75-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(2-hydroxy-4-isopropyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one
• 英文别名: 3-(2-hydroxy-6-oxo-4-propan-2-ylcyclohexen-1-yl)-3H-2-benzofuran-1-one
• CAS: 1434878-75-7
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: AAFBKWAFOMHXNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxy-4-isopropyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one 在 mercury(II) diacetate 、 sodium acetate 、 溶剂黄146 、 盐酸 作用下， 以 水 为溶剂， 反应 5.25h， 以94%的产率得到3-(2,6-dihydroxy-4-isopropylphenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones

  摘要：

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。

  DOI：

  10.3390/molecules18021881
• 作为产物：
  描述：

  3-羟基异苯并呋喃-1(3H)-酮 、 5-异丙基-1,3-环己二酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 7.08h， 以69%的产率得到3-(2-hydroxy-4-isopropyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones

  摘要：

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。

  DOI：

  10.3390/molecules18021881

文献信息

• Synthetic Analogues of the Natural Compound Cryphonectric Acid Interfere with Photosynthetic Machinery through Two Different Mechanisms
  作者：Róbson Ricardo Teixeira、Wagner Luiz Pereira、Deborah Campos Tomaz、Fabrício Marques de Oliveira、Samuele Giberti、Giuseppe Forlani

  DOI：10.1021/jf400698j

  日期：2013.6.12

  A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatization, and acetylation reactions. The measurement of the electron transport chain in spinach chloroplasts showed that several derivatives are capable of interfering with the photosynthetic apparatus. Few of them were found to inhibit the basal rate, but a significant inhibition was brought about only at concentrations exceeding 50 mu M. Some other analogues acted as uncouplers or energy transfer inhibitors, with a remarkably higher effectiveness. Isobenzofuranone addition to the culture medium inhibited the growth of the cyanobacterium,Synechococcus elongatus, with patterns consistent with the effects measured in vitro upon isolated chloroplasts. The most active derivatives, being able to completely suppress algal growth at 20 mu M, may represent structures to be exploited for the design of new active ingredients for weed control.
• Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones
  作者：Róbson Teixeira、Gustavo Bressan、Wagner Pereira、Joana Ferreira、Fabrício de Oliveira、Deborah Thomaz

  DOI：10.3390/molecules18021881

  日期：——

  A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。
• The Antileishmanial Potential of C-3 Functionalized Isobenzofuranones against Leishmania (Leishmania) Infantum Chagasi
  作者：Wagner Pereira、Raphael de Souza Vasconcellos、Christiane Mariotini-Moura、Rodrigo Saar Gomes、Rafaela Firmino、Adalberto da Silva、Abelardo Silva Júnior、Gustavo Bressan、Márcia Almeida、Luís Crocco Afonso、Róbson Teixeira、Juliana Lopes Rangel Fietto

  DOI：10.3390/molecules201219857

  日期：——

  Leishmaniases are diseases caused by protozoan parasites of the genus Leishmania. Clinically, leishmaniases range from cutaneous to visceral forms, with estimated global incidences of 1.2 and 0.4 million cases per year, respectively. The treatment of these diseases relies on multiple parenteral injections with pentavalent antimonials or amphotericin B. However, these pharmaceuticals are either too toxic or expensive for routine use in developing countries. These facts call for safer, cheaper, and more effective new antileishmanial drugs. In this investigation, we describe the results of the assessment of the activities of a series of isobenzofuran-1(3H)-ones (phtalides) against Leishmania (Leishmania) infantum chagasi, which is the main causative agent of visceral leishmaniasis in the New World. The compounds were tested at concentrations of 100, 75, 50, 25 and 6.25 µM over 24, 48, and 72 h. After 48 h of treatment at the 100 µM concentration, compounds 7 and 8 decreased parasite viability to 4% and 6%, respectively. The concentration that gives half-maximal responses (LC50) for the antileishmanial activities of compounds 7 and 8 against promastigotes after 24 h were 60.48 and 65.93 µM, respectively. Additionally, compounds 7 and 8 significantly reduced parasite infection in macrophages.

  利什曼病是由利什曼属的原生动物寄生虫引起的疾病。临床上，利什曼病从皮肤型到内脏型不等，全球估计每年分别有120万和40万例病例。这些疾病的治疗依赖于多次静脉注射五价锑或两性霉素B。然而，这些药物要么毒性过大，要么价格昂贵，不适宜在发展中国家常规使用。这些事实呼吁更安全、更廉价、更有效的新型抗利什曼药物。在本研究中，我们描述了评估一系列异苯并呋喃-1(3H)-酮（酞类）对利什曼原虫（Leishmania）婴儿型查加斯菌活性结果，该菌是新大陆内脏利什曼病的主要致病因子。这些化合物在100、75、50、25和6.25微摩尔浓度下分别测试了24、48和72小时。经过100微摩尔浓度下48小时的治疗后，化合物7和8分别将寄生虫存活率降低到4%和6%。在24小时后，化合物7和8对前鞭毛体的半最大效应浓度（LC50）分别是60.48和65.93微摩尔。此外，化合物7和8显著减少了巨噬细胞中的寄生虫感染。